Founding Enterprise Account Executive (Outbound & Growth) — Novilo

15Rock; Toronto; On-site; CAD 110,000 - 200,000; Full time

Job summary

Novilo, built by 15Rock, is seeking a Founding Enterprise Account Executive to build and scale outbound revenue against enterprise clients in a Toronto-based market. You will own high-velocity discovery, pilot programs, and ROI-driven closes with senior executives.

You will drive 4–6+ meetings weekly, prospect into named accounts, and partner with founders to shape territory strategy and channel relationships. This role offers significant upside in a fast-moving, frontier product space.

Qualifications

• 4–8+ years of full-cycle B2B enterprise software sales.
• 2+ years in an early-stage (Seed to Series B) environment.
• Self-sourced 60%–75%+ of closed new-logo revenue.
• Experience selling complex workflow, intelligence, procurement, or applied AI software.
• Executive-ready written communication (short, skimmable outreach).

Responsibilities

• Generate 4–6+ qualified discovery/pilot meetings per week via multi-threaded outreach (phone, email, LinkedIn, intros).
• Lead unscripted first-call conversations with senior stakeholders (Managing Partners, Proposal/Capture Leads, CISOs).
• Guide prospects into 15-day live RFP pilots and convert ROI into enterprise contracts.
• Expand adoption across sibling practice areas, regional offices, and additional modules.
• Build repeatable referral and co-selling relationships with channel partners.

Skills

Self-sourced sales

Enterprise software sales

New logo acquisition

Quota attainment

Executive communication

Job description

Employment Type:

Full-Time

About Novilo

Enterprise consulting, engineering, and infrastructure firms spend thousands of unbillable hours every year chasing complex, 200-page RFPs. Generic AI chat tools break on these pursuits—they hallucinate credentials, miss mandatory compliance gates, and fail enterprise security reviews.

Built by 15Rock, Novilo (novilo.ai) is an enterprise AI platform purpose-built for pre-tender discovery, RFP intelligence, and proposal automation. Our engine combines live tender radar, deterministic compliance cross-referencing, shadow scorecard evaluation, and verbatim source verification inside dedicated, single-tenant cloud infrastructure.

We aren't pre-product: Novilo is already in production with consulting, infrastructure, and enterprise advisory teams—cutting bid cycle costs by ~64% and saving ~39 hours per pursuit. Now, we are hiring a Founding Enterprise Account Executive to build and scale our outbound revenue engine alongside our CEO and Product Lead.

Who This Role Is (And Isn’t) For

We want to be upfront about what success looks like at our current stage:

• This IS for you if you love the zero-to-one hunt—breaking into named accounts from scratch (~70% new-logo outbound), running sharp discovery with Managing Partners and Capture Directors, and turning initial pilots into firm-wide deployments (~30% account expansion).
• This is NOT for you if you are looking to step away from outbound prospecting into pure account management/renewals, rely on an army of SDRs and inbound demo queues to fill your calendar, or need a rigid big-tech playbook before picking up the phone.

What You’ll Own

• Signal-Led Outbound Hunting (~70%): Build your own target account lists and generate 4–6+ qualified discovery/pilot meetings per week through concise, multi-threaded outreach (phone, bespoke email, LinkedIn, and warm network intros) anchored in live public tenders, capital budgets, and bid activity.
• Technical & Executive Discovery: Lead unscripted first-call conversations and live RFP walkthroughs with Managing Partners, Proposal/Capture Leads, and CISOs—credibly explaining why stateful compliance reasoning and isolated cloud deployments beat off-the-shelf LLM wrappers.
• High-Velocity Proof-of-Value (POV) Closing: Guide prospects into scoped, 15-day live RFP pilots and convert validated ROI into five- and six-figure annual enterprise contracts ($30K–$250K+ ACV).
• Land-and-Expand Growth (~30%): Treat the first signed contract as the starting line. Partner with practice leads and champions to expand adoption across sibling practice areas, regional offices, and additional Novilo modules.
• Channel Partner Activation: Build repeatable referral and co-selling relationships with independent RFP, capture, and procurement consultants.

What You Bring

• Proven Self-Sourced Track Record: 4–8+ years of full-cycle B2B enterprise software sales experience, including 2+ years in an early-stage (Seed to Series B) environment where you personally self-sourced 60%–75%+ of your closed new-logo revenue.
• Domain & Buyer Fluency: Experience selling complex workflow, intelligence, procurement, legal, or applied AI software into partnership-led or conservative enterprises (management consulting, engineering/infrastructure, IT advisory, or institutional financial services).
• Technical Curiosity: You don't treat software architecture or security reviews as a "black box." You can hold your own discussing data isolation, SharePoint/Microsoft Graph integrations, SOC 2 controls, and private cloud deployments without needing an engineer on every intro call.
• Consultative Commercial Rigor: History of 100%+ quota attainment on land-and-expand deals, crisp forecasting hygiene, and executive-ready written communication (short, skimmable outreach—never high-volume "spray and pray" sequences).

Why Join Us

• Sell a Live, High-ROI Product: Onboard clients onto real target RFPs in ~15 days with immediate, measurable pursuit economics rather than selling vapourware or 9-month implementations.
• Direct Founder Access & GTM Ownership: Work directly with the CEO and Product Lead with zero bureaucracy, fast product iteration loops, and direct influence over territory, pricing, and commercial strategy.
• Uncapped Upside: Ground-floor seat capturing marquee consulting and infrastructure logos with clear runway to grow into commercial leadership as the team scales.